Chichester was born in London and educated at Westminster School and Christ Church, Oxford. Since 1969 He has worked in family business Francis Chichester Ltd (publishers of maps, guides and educational wallcharts), founded by his father Sir Francis Chichester KBE, and still lives in the family home at 9 St James's Place, London SW1.

On 5 June 2008, Chichester stepped down as Leader of the Conservative MEPs, after it was alleged that since 1996 he had wrongly sent European parliamentary funds for secretarial and office services through his family business of which he was a paid director. He insists the contract was accepted by the EU Parliament 1999 and in 2004, he transferred money for his political staff through the company as an easier means of administration.[2][3] The European Parliament suggested that a change in the Financial Regulation in 2003 meant this arrangement constituted a potential conflict of interest.

David Cameron did not withdraw the party whip from him as he did with the former Conservative MP Derek Conway who then sat as an Independent. Chichester remained as a Conservative MEP but not their leader and was replaced by his deputy, Philip Bushill-Matthews. The revelation came while as Leader of the Conservative MEPs Cameron had tasked Chichester to review and compile a code of conduct for Conservative MEPs' expenses after the embarrassment of Derek Conway. However, Chichester admitted he had been told the contract was not in order so he cancelled it immediately and described it as a "whoopsy-daisy" surprise to him.[3] In September 2008 after a painstakingly detailed audit process by the European Parliament authorities Chichester received a letter from the Secretary General which cleared him of any conflict of interest, confirmed that all funds had been applied to the purpose intended and that he had received no personal benefit.